Indian Patents. 268494:A COMFORTABLE OPHTHALMIC DEVICE AND METHODS OF ITS PRODUCTION

Title of Invention	A COMFORTABLE OPHTHALMIC DEVICE AND METHODS OF ITS PRODUCTION
Abstract	This invention relates to comfortable ophthalmic devices and methods of producing.

Full Text	WO 2006/088758 PCT/US2006/004877 A COMFORTABLE OPHTHALMIC DEVICE AND METHODS OF ITS PRODUCTION RELATED APPLICATIONS This application is a non-provisional filing of two provisional applications, U.S. Serial No. 60/652,809, filed on February 14, 2005 and U.S. Serial No. 60/695,783 filed on June 30, 2005. FIELD OF THE INVENTION This invention relates to comfortable ophthalmic devices and methods of producing such devices. BACKGROUND Contact lenses have been used commercially to improve vision since the 1950s. The first contact lenses were made of hard materials. Although these lenses are currently used, they are not suitable for all patients due to their poor initial comfort. Later developments in the field gave rise to soft contact lenses, based upon hydrogels, which are extremely popular today. These lenses have higher oxygen permeabilities and such are often more comfortable to wear than contact lenses made of hard materials. However, these new lenses are not without problems. Contact lenses can be worn by many users for 8 hours to several days in a row without any adverse reactions such as redness, soreness, mucin buildup and symptoms of contact lens related dry eye. However, some users begin to develop these symptoms after only a few hours of use. Many of those contact lens wearers use rewetting solutions to alleviate discomfort associated with these adverse reactions with some success. However the use of these solutions require that users carry extra solutions and this can be inconvenient. For these users a more comfortable contact lens that does not require the use of rewetting solutions would be useful. Therefore there is a need for such contact lenses and methods of making such contact lenses. It is this need that is met by the following invention. BRIEF DESCRIPTION OF THE DRAWINGS Figure 1 Plot of the change in diameter of treated lenses versus control. 1 WO 2006/088758 PCT/US2006/004877 DETAILED DESCRIPTION OF THE INVENTION This invention includes a method of producing ophthalmic lenses comprising, consisting essentially of, or consisting of, treating a polymerized ophthalmic lens with a wetting agent, provided that the ophthalmic lens formulation does not comprise said wetting agent prior to its polymerization. As used herein, "ophthalmic lens" refers to a device that resides in or on the eye. These devices can provide optical correction or may be cosmetic. Ophthalmic lenses include but are not limited to soft contact lenses, intraocular lenses, overlay lenses, ocular inserts, and optical inserts. The preferred lenses of the invention are soft contact lenses made from silicone elastomers or hydrogels, which include but are not limited to silicone hydrogels, and fluorohydrogels. Soft contact lens formulations are disclosed in US Patent No. 5,710,302, WO 9421698, EP 406161, JP 2000016905, U.S. Pat. No. 5,998,498, U.S. Patent No. 6,087,415, U.S. Pat. No. 5,760,100, U.S. Pat. No.5,776, 999, U.S. Pat. No. 5,789,461, U.S. Pat. No. 5,849,811, and U.S. Pat. No. 5,965,631. The foregoing references are hereby incorporated by reference in their entirety. The particularly preferred ophthalmic lenses of the inventions are known by the United States Approved Names of acofilcon A, alofilcon A, alphafilcon A, amifilcon A, astifilcon A, atalafilcon A, balafilcon A, bisfilcon A, bufilcon A, comfilcon, crofilcon A, cyclofiicon A, darfilcon A, deltafilcon A, deltafilcon B, dimefilcon A, drooxifilcon A, epsifilcon A, esterifilcon A, etafilcon A, focofilcon A, genfilcon A, govafilcon A, hefilcon A, hefilcon B, hefilcon D, hilafilcon A, hilafilcon B, hioxifilcon B, hioxifilcon C, hixoifilcon A, hydrofilcon A, lenefilcon A, licryfilcon A, licryfilcon B, lidofilcon A, lidofilcon B, lotrafilcon A, lotrafilcon B, mafilcon A, mesifilcon A, methafiicon B, mipafilcon A, nelfilcon A, netrafilcon A, ocufilcon A, ocufilcon B, ocufilcon C, ocufilcon D, ocufilcon E, ofilcon A, omafilcon A, oxyfilcon A, pentafilcon A, perfilcon A, pevafilcon A, phemfilcon A, polymacon, silafilcon A, siloxyfilcon A, tefilcon A, tetrafilcon A, trifilcon A, and xylofilcon A. More particularly preferred ophthalmic lenses of the invention are genfilcon A, lenefilcon A, comfilcon, lotrafilcon A, lotraifilcon B, and balafilcon A. The most preferred lenses include etafilcon A, nelfilcon A, hilafilcon, and polymacon. 2 WO 2006/088758 PCT/US2006/004877 The term "formulation" refers to the un-po!ymerized mixture of components used to prepare ophthalmic lenses. These components include but are not limited to monomers, pre-polymers, diluents, catalysts, initiators tints, UV blockers, antibacterial agents, polymerization inhibitors, and the like. These formulations can be polymerized, by thermal, chemical, and light initiated curing techniques described in the foregoing references as well as other references in the ophthalmic lens field. As used herein, the terms "polymerized" or "polymerization" refers to these processes. The preferred methods of polymerization are the light initiated techniques disclosed in U.S. Pat. No. 6,822,016 which is hereby incorporated by reference in its entirety. As used herein the term "treating" refers to physical methods of contacting the wetting agents and the ophthalmic lens. These methods exclude placing a drop of a solution containing wetting agent into the eye of an ophthalmic lens wearer or placing a drop of such a solution onto an ophthalmic lens prior to insertion of that lens into the eye of a user. Preferably treating refers to physical methods of contacting the wetting agents with the ophthalmic lenses prior to selling or otherwise delivering the ophthalmic lenses to a patient. The ophthalmic lenses may be treated with the wetting agent anytime after they are polymerized. It is preferred that the polymerized ophthalmic lenses be treated with wetting agents at temperature of greater than about 50°C. For example in some processes to manufacture contact lenses, an un-polymerized, or partially polymerized formulation is placed between two mold halves, spincasted, or static casted and polymerized. See, U.S. Pat. Nos. 4,495,313; 4,680,336; 4,889,664, 3,408.429; 3,660,545; 4,113,224; and 4,197,266, all of which are incorporated by reference in their entirety. In the case of hydrogels, the ophthalmic lens formulation is a hardened disc that is subjected to a number of different processing steps including treating the polymerized ophthalmic lens with liquids (such as water, inorganic salts, or organic solutions) to swell, or otherwise equilibrate this polymerized ophthalmic lens prior to enclosing the polymerized ophthalmic lens in its final packaging. Polymerized ophthalmic lenses that have not been swelled or otherwise equilibrated are known as un-hydrated polymerized ophthalmic lenses. The addition of the wetting agent to any of the liquids of this "swelling or 3 WO 2006/088758 PCT/US2006/004877 "equilibrating" step at room temperature or below is considered "treating" the lenses with wetting agents as contemplated by this invention. In addition, the polymerized un-hydrated ophthalmic lenses may be heated above room temperature with the wetting agent during swelling or equilibrating steps. The preferred temperature range is from about 50°C for about 15 minutes to about sterilization conditions as described below, more preferably from about 50°C to about 85°C for about 5 minutes. Yet another method of treating is physically contacting polymerized ophthalmic lens (either hydrated or un-hydrated) with a wetting agent at between about room temperature and about 85°C for about 1 minute to about 72 hours, preferably about 24 to about 72 hours, followed by physically contacting the polymerized ophthalmic lens with a wetting agent at between about 85°C and 150°C for about 15 minutes to about one hour. Many ophthalmic lenses are packaged in individual blister packages, and sealed prior to dispensing the lenses to users. As used herein, these polymerized lenses are referred to as "hydrated polymerized ophthalmic lenses". Examples of blister packages and sterilization techniques are disclosed in the following references which are hereby incorporated by reference in their entirety, U.S. Pat. Nos. D435.966 S; 4,691,820; 5,467,868; 5,704,468; 5,823,327; 6,050,398, 5,696,686; 6,018,931; 5,577,367; and 5,488,815. This portion of the manufacturing process presents another method of treating the ophthalmic lenses with wetting agents, namely adding wetting agents to packaging solution prior to sealing the package, and subsequently sterilizing the package. This is the preferred method of treating ophthalmic lenses with wetting agents. Sterilization can take place at different temperatures and periods of time. The preferred sterilization conditions range from about 100°C for about 8 hours to about 150°C for about 0.5 minute. More preferred sterilization conditions range from about 115°C for about 2.5 hours to about 130°C for about 5.0 minutes. The most preferred sterilization conditions are about 124°C for about 30 minutes. The "packaging solutions" that are used in methods of this invention may be water-based solutions. Typical packaging solutions include, without 4 WO 2006/088758 PC I7US2006/004877 limitation, saline solutions, other buffered solutions, and deionized water. The preferred aqueous solution is deioinized water or saline solution containing salts including, without limitation, sodium chloride, sodium borate, sodium phosphate, sodium hydrogenphosphate, sodium dihydrogenphosphate, or the corresponding potassium salts of the same. These ingredients are generally combined to form buffered solutions that include an acid and its conjugate base, so that addition of acids and bases cause only a relatively small change in pH. The buffered solutions may additionally include 2-(N- morpholino)ethanesulfonic acid (MES), sodium hydroxide, 2,2- bis(hydroxymethyl)-2,2',2"-nitrilotriethanol, n-tris(hydroxymethyl)methyl-2- aminoethanesulfonic acid, citric acid, sodium citrate, sodium carbonate, sodium bicarbonate, acetic acid, sodium acetate, ethylenediamine tetraacetic acid and the like and combinations thereof. Preferably, the packaging solution is a borate buffered or phosphate buffered saline solution or deionized water. The particularly preferred packaging solution contains about 1,850 ppm to about 18,500 ppm sodium borate, most particularly preferred about 3,700 ppm of sodium borate. As used here, the term "wetting agent" refers polymers having a number average molecular weight of about at least 500, that impart a moist feeling when added to the eyes of contact lens wearers. Examples of preferred wetting agents include but are not limited to poly(meth)acrylamides [i.e.poly N,N-dimethylacry!amide), poly (N-methylacrylamide) poly (acrylamide), poly(N-2-hydroxyethylmethacrylamide), and poly(glucosamineacrylamide)], poly(itaconic acid), hyaluronic acid, xanthan gum, gum Arabic (acacia), starch, polymers of hydroxylalkyl(meth)acrylates [i.e. poly( 2- hydroxyethylmethacrylate), poly(2,3-dihydroxypropylmethacrylate, and poly(2- hydroxyethylacrylate)], and polyvinylpyrrolidone. Additional preferred wetting agents include but are not limited to co- polymers and graft co-polymers of the aforementioned preferred wetting agents, such co-polymers and graft co-polymers include repeating units of hydrophilic or hydrophobic monomers, preferably in amounts of about less than ten percent by weight, more preferably less than about two percent. Such repeating units of hydrophilic or hydrophobic monomers include but are not 5 WO 2006/088758PCT/US2006/004877 limited to alkenes, styrenes, cyclic N-vinyl amides, acrylamides, hydroxyalkyl (meth) acrylates, alkyl (meth) acrylates, siloxane substituted acrylates, and siloxane substituted methacrylates. Specific examples of hydrophilic or hydrophobic monomers which may be used to form the above co-polymers and graft co-polymers include but are not limited to ethylene, styrene, N- vinylpyrrolidone, N,N-dimethylacrylamide, 2-hydroxyethylmethyacrylate, methyl methacrylate and butyl methacrylate, methacryloxypropyl tristrimethylsiloxysilane and the like. The preferred repeating units of hydrophilic or hydrophobic monomers are N-vinylpyrrolidone, N,N- dimethylacrylamide, 2-hydroxyethylmethacrylate, methyl methacrylate, and mixtures thereof. Further examples of wetting agents include but are not limited to polymers with carbon backbones and pendant polyethylene glycol chains [i.e. polymers of polyethylene glycol monoomethacrylate] copolymers of ethylene glycol [copolymers with 1,2,propyleneglycol, 1,3-propylene glycol, methyleneglycol, and tetramethylene glycol]. The preferred wetting agents are polyvinylpyrrolidone, graft co-polymers and co-polymers of polyvinylpyrrolidone, the particularly preferred wetting agent is polyvinylpyrrolidone. Polyvinylpyrrolidone ("PVP") is the polymerization product of N-vinyipyrrolidone. PVP is available in a variety of molecular weights from about 500 to about 6,000,000 Daltons. These molecular weights can be expressed in term of K- values, based on kinematic viscosity measurements as described in Encyclopedia of Polymer Science and Engineering, John Wiley & Sons Inc, and will be expressed in these numbers throughout this application. The use of PVP having the following K-values from about K-30 to about K-120 is contemplated by this invention. The more preferred K-values are about K-60 to about K-100, most preferably about K-80 to about K-100. For the treatment of etafilcon A lenses, the particularly preferred K-value of PVP is about K-80 to about K-95, more preferably about K-85 to about K-95, most preferably about K-90. The wetting agents can be added to the packaging solution at a variety of different concentrations such as about 100 ppm to about 150,000 ppm. For example if the wetting agents are added to packaging solutions containing un- hydrated polymerized ophthalmic lenses, the wetting agents are preferably 6 WO 2006/088758 PCT/US2006/004877 present at a concentration of about 30,000 ppm to about 150,000 ppm. If the wetting agents are added to packaging solutions containing hydrated polymerized ophthalmic lenses, the wetting agents are preferably present at a concentration of about 100 ppm, to about 3000 ppm, more preferably about 200 ppm to about 1000 ppm, most preferably less than about 500 ppm. For example when etafilcon A lenses are used in this invention and the wetting agent is K-90 PVP, the preferred packaging solution concentration of PVP K-90 is about 250ppm to about 2,500 ppm, more preferably about 300 to about 500 ppm, most preferably about 350 to about 440 ppm. When etafilcon A contact lenses are heated with K-90 PVP at a temperature greater than about 120°C for about 30 minutes at a concentration of about 400 to about 500 ppm, the treated lenses are more comfortable to users than untreated lenses. Further, this particular molecular weight and concentration of PVP does not distort or shift the diameter of the lenses during the treatment cycle or distort the users vision. While not wishing to be bound by any particular mechanism of incorporation, it is known that K-90 PVP is incorporated into the matrix of the lens after it is treated with K-90 PVP. In an etafilcon A contact lens, the preferred amount of incorporated K-90 PVP is about 0.01 mg to about 1.0 mg, more preferred about 0.10 mg to about 0.30 mg, most particularly preferred about 0.10 mg to about 0.20 mg. Lenses that have been treated in this manner are worn by users for up to 12 hours still maintain the incorporated PVP. Further the invention includes an ocular device comprising, consisting essentially of, or consisting of a polymerized ophthalmic lens wherein said polymerized ophthalmic lens is treated with a wetting agent, provided that the ophthalmic lens formulation does not comprise said wetting agent prior to its polymerization. The terms "ophthalmic lens," "wetting agent," "polymerized," and "formulation" all have their aforementioned meanings and preferred ranges. The term "treated" has the equivalent meaning and preferred ranges as the term treating. Still further the invention includes an ocular device prepared by treating a polymerized ophthalmic lens with a wetting agent, provided that the ophthalmic lens formulation does not comprise said wetting agent prior to its 7 WO 2006/088758PCT/US2006/004877 polymerization. The terms "ophthalmic lens," "wetting agent," "polymerized," "treated" and "formulation" all have their aforementioned meanings and preferred ranges. The application of the invention is described in further detail by use of the following examples. These examples are not meant to limit the invention, only to illustrate its use. Other modifications that are considered to be within the scope of the invention, and will be apparent to those of the appropriate skill level in view of the foregoing text and following examples. EXAMPLES Example 1 Cured etafilcon A contact lenses (sold as 1-Day Acuvue® brand contact lenses by Johnson & Johnson Vision Care, Inc.) were equilibrated in deionized water, and packaged in solutions containing PVP in borate buffered saline solution ((lOOOmL, sodium chloride 3.55g, sodium borate 1.85 g, boric acid 9.26 g, and ethylenediamine tetraacetic acid 0.1 g: 5 rinses over 24 hours, 950 + uL), sealed with a foil lid stock, and sterilized (121°C, 30 minutes). Before the addition of PVP each solution contained water, l000mL, sodium chloride 3.55g, sodium borate 1.85 g, boric acid, 9.26 g, and ethylenediamine tetraacetic acid 0.1g. A variety of different weights and concentrations of PVP were used as shown in Table 1, below The amount of PVP that is incorporated into each lens is determined by removing the lenses from the packaging solution and extracting them with a mixture 1:1 mixture of N,N-dimethylforamide, (DMF) and deionized water (Dl). The extracts are evaluated by high performance liquid chromatography (HPLC). Three lenses were used for each evaluation. The results and their standard deviation are presented in Table 1. 8 WO 2006/088758PCT/US2006/004877 Table 1 Sample # Type of PVP Cone, (ppm) mg of PVPin lens Control None None none 1 K-12 3000 0.24(0.01) 2 K-12 20,000 1.02(0.01) 3 K-30 1500 1.39(0.05) 4 K-30 2000 1.50(0.01) 5 K-60 1000 0.56(0.00) 6 K-60 1500 0.85(0.02) 7 K-60 2500 1.02(0.03) 8 K-90 250 0.10(0.00) 9 K-90 500 0.14(0.00) 10 K-90 1000 0.2(0.01) 11 K-90 2500 0.25 (0.02) 12 K-120 500 0.07 (0.00) Example 2 Samples of treated etafilcon A lenses were prepared via the treatment and sterilization methods of Example 1 from K-12, K-30, K-60, K-90, and K-120 PVP at concentrations of 0.30%, 1.65%, and 3.00%. After sterilization, the diameter of the lenses was, compared to an untreated lens and evaluated to determine if the process changed those diameters. The results, Figure 1, plot the change in diameter vs the type of PVP at a particular concentration. This data shows that K-12, K-90, and K-120 have a minimal effect on the diameter of the lenses. Example 3 Several etafilcon A lenses were treated with K-90 PVP at a concentration of 500 ppm and sterilized according to the methods of Example 1. The lenses were stored in their packages for approximately 28 days at room temperature and were then measured for diameter, base curve, sphere power, and center thickness. Thereafter, lenses were heated at 55°C for one month. The diameter, base curve, sphere power, and center thickness of the lenses was measured and the results were evaluated against an untreated lens and data is presented in Table 2. This data illustrates that the parameters of lenses treated with K-90 PVP are not significantly affected by time at elevated temperature. 9 WO 2006/4)88758PCT/US2006/004877 Table 2 Baseline Change from Baseline of Sample after one month storage at 55 °C Diameter (mm) 14.37(0.02) 0.02 Base curve (mm) 8.90 (0.03) -0.01 Power (diopter) -0.75 (0.05) 0.00 Center Thickness 0.127(0.005) 0.002 (mm) Example 4 Etafilcon-A lenses treated with PVP K-90 at a concentration of 440ppm and sterilized (124°C, approximately 18 minutes) were sampled from manufacturing lines and measured for diameter, base curve, sphere power, and center thickness and compared to similar measurements made on untreated 1-Day Acuvue® brand lenses. The data presented in Table 3 illustrates that K-90 PVP does not significantly affect these parameters. Table 3 Treated Untreated Diameter (mm) 14.24 (0.04) 14.18(0.04) Base curve (mm) 8.94 (0.03) 8.94 (0.04) Sphere Power Deviation fromTarget (diopter) -0.01 (0.04) -0.02 (0.04) Center Thickness Deviationfrom Target (mm) 0.000 (0.004) 0.002 (0.005) 10 WO 2006/088758PCT/US2006/004877 Example 5 Etafilcon A lenses were prepared according to Example 1 at the concentrations of Table 1. The treated lenses were clinically evaluated in a double-masked studies of between 9 and 50 patients. The patients wore the lenses in both eyes for 3-4 days with overnight removal and daily replacement, and wore untreated 1-Day Acuvue® brand contact lenses for 3-4 days with overnight removal and daily replacement as a control. Patients were not allowed to use rewetting drops with either type of lens. Patients were asked to rate the lens using a questionnaire. All patients were asked a series of questions relating to overall preference, comfort preference, end of day preference, and dryness. In their answers they were asked to distinguish if they preferred the treated lens, the 1-Day control lens, both lenses or neither lens. The results are shown in Tables 4 and 5. The numbers in the columns represent the percentage of patients that positively responded to each of the four options. The "n" number represents the number of patients for a particular sample type. "DNT" means did not test and n/a means non applicable. The numbers illustrate that lenses treated with K-90 PVP at a concentration of about 500 ppm have good clinical comfort on the eye. The sample # refers to the sample numbers in Table 1. Table 4 Overall Preference, % Comfort Preference, % Sample # n PVPtreated 1-Day Both Neither PVPtreated 1-Day Both Neither 1 9 67 22 11 0 67 22 11 0 2 37 27 49 22 3 30 46 19 5 3 41 34 49 15 2 27 56 12 5 4 10 30 20 50 0 30 40 30 0 5 41 27 61 10 2 22 49 29 0 6 42 33 33 33 0 33 29 38 0 7 37 51 27 19 3 49 11 38 3 8 41 27 37 32 5 24 34 37 5 9 48 33 27 40 0 33 23 44 0 10 45 18 27 51 4 16 20 58 7 11 WO 2006/088758PCT/US2006/004877 Table 5 Dryness Preference % End of Day Preference % Sample # n PVPtreated 1-Day Both Neither PVPtreated 1-Day Both Neither 1 9 33 33 11 0 56 22 44 0 2 37 24 43 22 8 27 43 27 5 3 41 32 51 17 2 29 49 17 2 4 10 20 40 30 10 20 10 60 10 5 41 20 46 32 2 20 41 37 2 6 31 42 24 38 0 38 35 16 6 7 42 36 19 38 3 41 24 40 0 8 41 27 22 49 7 22 24 41 7 9 48 38 21 46 0 33 19 44 0 10 45 24 20 58 4 18 20 51 4 Example 6 An etafilcon A contact lens was treated with 500ppm of K-90 PVP using the methods of Example 1. The treated lenses were briefly rinsed with phosphate buffered saline solution and rinsed lenses were placed in the well of a cell culture cluster container (Cellgrow XL) that mimics the dimensions of a human eye. See, Farris RL, Tear Analysis in Contact Lens Wears, Tr. Am. Opth. Soc. Vol. LXXXIII, 1985. Four hundred microliters of phosphate buffered saline solution (KH2PO4 0.20 g/L, KCI- 0.20 g/L, NaCI 8.0 g/L, Na2HPO4 [anhydrous] 1.15 g/L) was added to each container. The wells were covered and the container was stored in an oven at 35°C. Three lenses were removed from the oven at various times and analyzed by HPLC to determine whether PVP was released into the phosphate buffered saline solution. The average results are presented in Table 6. The limit of quantification for PVP is 20 ppm. The test did not detect any PVP in the analyzed samples. This data shows that PVP is not released at levels greater than 20ppm. 12 WO 2006/088758 PCT/US2006/004877 Tab le 6 Time PVPReleased 30 min. 1 hr. 2hr. 4hr. 8hr. 16 hr. 24 hr 13 WO 2006/088758 PCT/US2006/004877 What is claimed is 1. A method of producing ophthalmic lenses comprising, treating a polymerized ophthalmic lens with a wetting agent, provided that the ophthalmic lens formulation does not comprise said wetting agent prior to its polymerization. 2. The method of claim 1 wherein treating comprises heating the polymerized ophthalmic lens in a packaging solution. 3. The method of claim 2 wherein the polymerized ophthalmic lens is heated to a temperature of at least about greater than 50°C to about 150°C. 4. The method of claim 1 wherein the packaging solution comprises deionized water, or saline solution. 5. The method of claim 1 wherein the packaging solution comprises about 1870 ppm to about 18,700 ppm sodium borate 6. The method of claim 1 wherein the packaging solution comprises about 3700 ppm sodium borate. 7. The method of claim 1 wherein the packaging solution comprises about 2000 ppm to about 5000 ppm sodium borate. 8. The method of claim 1 wherein the wetting agent is selected from the group consisting of poly(meth)acrylamides, poly(itaconic acid), hyaluronic acid, xanthan gum, gum Arabic, starch, polymers of hydroxyla!kyl(meth)acrylates, and polyvinylpyrrolidone. 9. The method of claim 1 wherein the wetting agent is selected from the group consisting of polyvinylpyrrolidone, graft co-polymers of polyvinylpyrrolidone, and co-polymers of polyvinylpyrrolidone. 14 WO 2006/088758PCT/US2006/004877 10. The method of claim 1 wherein the wetting agent is polyvinylpyrrolidone. 11. The method of claim 10 wherein the K-value of the polyvinylpyrrolidone is about K-60 to about K-120. 12. The method of claim 10 wherein the K-value of the polyvinylpyrrolidone is about K-85 to about K-95. 13. The method of claim 10 wherein the K-value of polyvinylpyrrolidone is about K-90. 14. The method of claim 1 wherein treating comprises heating the polymerized ophthalmic lens in a packaging solution comprising polyvinylpyrrolidone having a K-value of about K-85 to about K-95 at a temperature of greater than about 80°C. 15. The method of claim 1 wherein treating comprises heating the polymerized ophthalmic lens in a packaging solution comprising polyvinylpyrrolidone having a K-value of about K-85 to about K-95 at a temperature of greater than about 120°C. 16. The method of claim 2 wherein the wetting agent is polyvinylpyrrolidone and the concentration of polyvinylpyrrolidone in the packaging solution is about 250 ppm to about 2500 ppm. 17. The method of claim 2 wherein the concentration of wetting agent in the packaging solution is about 100 ppm to about 3000 ppm. 18. The method of claim 1 wherein the polymerized ophthalmic lens is heated at about 124°C for about 18 minutes and with polyvinylpyrrolidone having a K-value of about K-90 at a concentration of about 400 to about 440 ppm. 15 WO 2006/088758PCT/US2006/004877 19. The method of claim 1 wherein the polymerized ophthalmic lens is heated at about 121 °C for about 30 minutes and with polyvinylpyrrolidone having a K-value of about K-90 at a concentration of about 300 to about 400 ppm. 20. The method of claim 2 wherein the treating step is conducted in an individual sealed contact lens package. 21. The method of claim 17 wherein the treating step is conducted in an individual sealed contact lens package. 22. The method of claim 18 wherein the treating step is conducted in an individual sealed contact lens package. 23. The method of claim 1 wherein the ophthalmic lens is selected from the group consisting of acofilcon A, alofilcon A, alphafilcon A, amifilcon A, astifilcon A, atalafilcon A, balafilcon A, bisfilcon A, bufilcon A, comfilcon, crofilcon A, cyclofilcon A, darfilcon A, deltafilcon A, deltafilcon B, dimefilcon A, drooxifilcon A, epsifilcon A, esterifilcon A, etafilcon A, focofilcon A, genfilcon A, govafilcon A, hefilcon A, hefilcon B, hefilcon D, hilafilcon A, hilafilcon B, hioxifilcon B, hioxifilcon C, hixoifilcon A, hydrofilcon A, lenefilcon A, licryfilcon A, licryfilcon B, lidofilcon A, lidofilcon B, lotrafilcon A, lotrafilcon B, mafilcon A, mesifilcon A, methafilcon B, mipafilcon A, nelfilcon A, netrafilcon A, ocufilcon A, ocufilcon B, ocufilcon C, ocufilcon D, ocufilcon E, ofilcon A, omafilcon A, oxyfilcon A, pentafilcon A, perfilcon A, pevafilcon A, phemfilcon A, polymacon, silafilcon A, siloxyfilcon A, tefilcon A, tetrafilcon A, trifilcon A, and xylofilcon A. 24. The method of claim 2 wherein the ophthalmic lens is selected from the group consisting of acofilcon A, alofilcon A, alphafilcon A, amifilcon A, astifilcon A, atalafilcon A, balafilcon A, bisfilcon A, bufilcon A, comfilcon, crofilcon A, cyclofilcon A, darfilcon A, deltafilcon A, deltafilcon B, dimefilcon A, drooxifilcon A, epsifilcon A, esterifilcon A, etafilcon A, focofilcon A, genfilcon A, govafilcon 16 WO 2006/088758PCT/US2006/004877 A, hefilcon A, hefilcon B, hefilcon D, hilafilcon A, hilafilcon B, hioxifilcon B, hioxifilcon C, hixoifilcon A, hydrofilcon A, lenefilcon A, licryfilcon A, licryfilcon B, lidofilcon A, lidofilcon B, lotrafilcon A, lotrafilcon B, mafilcon A, mesifilcon A, methafilcon B, mipafilcon A, nelfilcon A, netrafilcon A, ocufilcon A, ocufilcon B, ocufilcon C, ocufilcon D, ocufilcon E, ofilcon A, omafilcon A, oxyfilcon A, pentafilcon A, perfilcon A, pevafilcon A, phemfilcon A, polymacon, silafilcon A, siloxyfilcon A, tefilcon A, tetrafilcon A, trifilcon A, and xylofilcon A. 25. The method of claim 14 wherein the ophthalmic lens is selected from the group consisting of acofilcon A, alofilcon A, alphafilcon A, amifilcon A, astifilcon A, atalafilcon A, balafilcon A, bisfilcon A, bufilcon A, comfilcon, crofilcon A, cyclofilcon A, darfilcon A, deltafilcon A, deltafilcon B, dimefilcon A, drooxifilcon A, epsifilcon A, esterifilcon A, etafilcon A, focofilcon A, genfilcon A, govafilcon A, hefilcon A, hefilcon B, hefilcon D, hilafilcon A, hilafilcon B, hioxifilcon B, hioxifilcon C, hixoifilcon A, hydrofilcon A, lenefilcon A, licryfilcon A, licryfilcon B, lidofilcon A, lidofilcon B, lotrafilcon A, lotrafilcon B, mafilcon A, mesifilcon A, methafilcon B, mipafilcon A, nelfilcon A, netrafilcon A, ocufilcon A, ocufilcon B, ocufilcon C, ocufilcon D, ocufilcon E, ofilcon A, omafilcon A, oxyfilcon A, pentafilcon A, perfilcon A, pevafilcon A, phemfilcon A, polymacon, silafilcon A, siloxyfilcon A, tefilcon A, tetrafilcon A, trifilcon A, and xylofilcon A. 26. The method of claim 2 wherein the ophthalmic lens is selected from the group consisting of genfilcon A, lenefilcon A, lotrafilcon A, lotrafilcon B, balafilcon A, comfilcon, etafilcon A, nelfilcon A, hilafilcon, and polymacon. 27. The method of claim 14 wherein the ophthalmic lens is selected from the group consisting of genfilcon A, lenefilcon A, lotrafilcon A, lotrafilcon B, balafilcon A, comfilcon, etafilcon A, nelfilcon A, hilafilcon, and polymacon. 28. The method of claim 2 wherein the ophthalmic lens is selected from the group consisting of etafilcon A, nelfilcon A, hilafilcon, and polymacon. 17 WO 2006/088758 PCT/US2006/004877 29. The method of claim 14 wherein the ophthalmic lens is selected from the group consisting of etafilcon A, nelfilcon A, hilafilcon, and polymacon. 30. The method of claim 2 wherein the ophthalmic lens is selected from the group consisting of etafilcon A. 31. The method of claim 14 wherein the ophthalmic lens is selected from the group consisting of etafilcon A. 32. The method of claim 18 wherein the ophthalmic lens is an etafilcon A contact lens. 33. The method of claim 1 wherein the polymerized ophthalmic lens is an un-hydrated polymerized ophthalmic lens. 34. The method of claim 33 wherein treating comprises contacting the un- hydrated polymerized ophthalmic lens with a packaging solution comprises about 1870 ppm to about 18,700 ppm sodium borate. 35. The method of claim 33 wherein the treating further comprises heating the un-hydrated polymerized ophthalmic lens and packaging solution to a temperature of at least about 50°C to about 100°C. 36. The method of claim 33 wherein the treating further comprises maintaining the un-hydrated polymerized ophthalmic lens and packaging solution at a temperature of at least about 10°C to about room temperature. 37. The method of claim 34 wherein the packaging solution further comprises deionized water, or saline solution. 38. The method of claim 33 wherein the wetting agent is selected from the group consisting of poly(meth)acrylamides, poly(itaconic acid), hyaluronic acid, 18 WO 2006/088758 PCT/US2006/004877 xanthan gum, gum Arabic, starch, polymers of hydroxylalkyl(meth)acrylates, and polyvinylpyrrolidone. 39. The method of claim 33 wherein the wetting agent is selected from the group consisting of polyvinylpyrrolidone, graft co-polymers of polyvinylpyrrolidone, and co-polymers of polyvinylpyrrolidone. 40. The method of claim 33 wherein the wetting agent is polyvinylpyrrolidone. 41. The method of claim 33 wherein the K-value of the polyvinylpyrrolidone is about K-60 to about K-120. 42. The method of claim 33 wherein the K-value of the polyvinylpyrrolidone is about K-60 to about K-90. 43. The method of claim 40 wherein the polyvinylpyrrolidone is present at a concentration of about 30,000 ppm to about 150,000 ppm. 44. The method of claim 34, further comprising a second step of heating the un-hydrated polymerized ophthalmic lens of claim 34 with a second portion of packaging solution comprising a second wetting agent. 45. The method of claim 44 wherein the wetting agent is polyvinylpyrrolidone having a K-value of about K-60 and the second wetting agent is polyvinylpyrrolidone having a K-value of about K-90. 46. The method of claim 44 wherein the wetting agent is polyvinylpyrrolidone having a K-value of about K-90 and the second wetting agent is polyvinylpyrrolidone having a K-value of about K-90. 19 WO 2006/088758PCT/US2006/004877 47. The method of claim 45 wherein the concentration of K60 is between about 30,000 ppm and 150,000 about ppm and the concentration of K90 is between about 100 ppm and about 500 ppm. 48. An ocular device comprising a polymerized ophthalmic lens wherein said polymerized ophthalmic lens is treated with a wetting agent, provided that the ophthalmic lens formulation does not comprise said wetting agent prior to its polymerization. 49. The device of claim 48 wherein the wetting agent is selected from the group consisting of poly(meth)acry!amides, poly(itaconic acid), hyaluronic acid, xanthan gum, gum Arabic, starch, polymers of hydroxylalkyl(meth)acrylates, and polyvinylpyrrolidone. 50. The device of claim 48 wherein the wetting agent is polyvinylpyrrolidone, graft co-polymers of polyvinylpyrrolidone, and co-polymers of polyvinylpyrrolidone. 51. The device of claim 48 wherein the wetting agent is polyvinylpyrrolidone. 52. The device of claim 48 comprising about 0.01 mg to about 1.0 mg polyvinylpyrrolidone. 53. The device of claim 48 comprising about 0.10 mg to about 0.44 mg of polyvinylpyrrolidone. 54. The device of claim 48 wherein said device does not distort the user's vision. 55. The device of claim 48 comprising about 0.01 mg to about 1.0 mg of a wetting agent selected from the group consisting of poly(meth)acrylamides, poly(itaconic acid), hyaluronic acid, xanthan gum, gum Arabic, starch, polymers of hydroxylalkyl(meth)acrylates, and polyvinylpyrrolidone. 20 WO 2006/088758PCT/US2006/004877 56. The device of claim 48 comprising about 0.10 mg to about 0.44 mg of poly(meth)acrylamides, poly(itaconic acid), hyaluronic acid, xanthan gum, gum Arabic, starch, polymers of hydroxyla!kyl(meth)acrylates, and polyvinylpyrrolidone. 57. The device of claim 48 wherein said device does not distort the user's vision. 58. The device of claim 48 wherein said wetting agent remains in the ophthalmic lens after about 6 hours to about 24 hours of wear by a user. 59. An ocular device prepared by treating a polymerized ophthalmic lens with a wetting agent, provided that the ophthalmic lens formulation does not comprise said wetting agent prior to its polymerizaton. 60. The device of claim 59 wherein treating comprises heating the polymerized ophthalmic lens in a packaging solution to a temperature of about greater than 50°C to about 150°C. 61. The device of claim 59, wherein the wetting agent is selected from the group consisting of polyvinylpyrrolidone, graft co-polymers of polyvinylpyrrolidone, and co-polymers of polyvinylpyrrolidone. 62. The device of claim 59 wherein the wetting agent is polyvinylpyrrolidone having a K-value of about K-60 to about K-90. 63. The device claim 59 wherein the ophthalmic lens is selected from the group consisting of acofilcon A, alofilcon A, alphafilcon A, amifilcon A, astifilcon A, atalafilcon A, balafilcon A, bisfilcon A, bufilcon A, comfilcon, crofilcon A, cyclofilcon A, darfilcon A, deltafilcon A, deltafilcon B, dimefilcon A, drooxifilcon A, epsifilcon A, esterifilcon A, etafilcon A, focofilcon A, genfilcon A, govafilcon A, hefilcon A, hefilcon B, hefilcon D, hilafilcon A, hilafilcon B, hioxifilcon B, 21 WO 2006/088758 PCT/US2006/004877 hioxifilcon C, hixoifilcon A, hydrofilcon A, lenefilcon A, licryfilcon A, licryfilcon B, lidofilcon A, lidofilcon B, lotrafilcon A, lotrafilcon B, mafilcon A, mesifilcon A, methafilcon B, mipafilcon A, nelfilcon A, netrafilcon A, ocufilcon A, ocufilcon B, ocufilcon C, ocufilcon D, ocufilcon E, ofilcon A, omafilcon A, oxyfilcon A, pentafilcon A, perfilcon A, pevafilcon A, phemfilcon A, polymacon, silafilcon A, siloxyfilcon A, tefilcon A, tetrafilcon A, trifilcon A, and xylofilcon A. 22 64. The device of claim 59 wherein the ophthalmic lens is selected from the group consisting of genfilcon A, lenefilcon A, lotrafilcon A, lotrafilcon B, balifilcon A, comfilcon, etafilcon A, nelfilcon A, hilafilcon, and polymacon. 65. The device of claim 59 wherein the ophthalmic lens is etafilcon A. This invention relates to comfortable ophthalmic devices and methods of producing.

Full Text

WO 2006/088758 PCT/US2006/004877
A COMFORTABLE OPHTHALMIC DEVICE AND METHODS OF ITS
PRODUCTION
RELATED APPLICATIONS
This application is a non-provisional filing of two provisional applications,
U.S. Serial No. 60/652,809, filed on February 14, 2005 and U.S. Serial No.
60/695,783 filed on June 30, 2005.
FIELD OF THE INVENTION
This invention relates to comfortable ophthalmic devices and methods of
producing such devices.
BACKGROUND
Contact lenses have been used commercially to improve vision since the
1950s. The first contact lenses were made of hard materials. Although these
lenses are currently used, they are not suitable for all patients due to their poor
initial comfort. Later developments in the field gave rise to soft contact lenses,
based upon hydrogels, which are extremely popular today. These lenses have
higher oxygen permeabilities and such are often more comfortable to wear than
contact lenses made of hard materials. However, these new lenses are not
without problems.
Contact lenses can be worn by many users for 8 hours to several days
in a row without any adverse reactions such as redness, soreness, mucin
buildup and symptoms of contact lens related dry eye. However, some users
begin to develop these symptoms after only a few hours of use. Many of those
contact lens wearers use rewetting solutions to alleviate discomfort associated
with these adverse reactions with some success. However the use of these
solutions require that users carry extra solutions and this can be inconvenient.
For these users a more comfortable contact lens that does not require the use
of rewetting solutions would be useful. Therefore there is a need for such
contact lenses and methods of making such contact lenses. It is this need that
is met by the following invention.
BRIEF DESCRIPTION OF THE DRAWINGS
Figure 1 Plot of the change in diameter of treated lenses versus control.
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WO 2006/088758 PCT/US2006/004877
DETAILED DESCRIPTION OF THE INVENTION
This invention includes a method of producing ophthalmic lenses
comprising, consisting essentially of, or consisting of, treating a polymerized
ophthalmic lens with a wetting agent, provided that the ophthalmic lens
formulation does not comprise said wetting agent prior to its polymerization.
As used herein, "ophthalmic lens" refers to a device that resides in or on
the eye. These devices can provide optical correction or may be cosmetic.
Ophthalmic lenses include but are not limited to soft contact lenses, intraocular
lenses, overlay lenses, ocular inserts, and optical inserts. The preferred lenses
of the invention are soft contact lenses made from silicone elastomers or
hydrogels, which include but are not limited to silicone hydrogels, and
fluorohydrogels. Soft contact lens formulations are disclosed in US Patent No.
5,710,302, WO 9421698, EP 406161, JP 2000016905, U.S. Pat. No.
5,998,498, U.S. Patent No. 6,087,415, U.S. Pat. No. 5,760,100, U.S. Pat.
No.5,776, 999, U.S. Pat. No. 5,789,461, U.S. Pat. No. 5,849,811, and U.S. Pat.
No. 5,965,631. The foregoing references are hereby incorporated by reference
in their entirety. The particularly preferred ophthalmic lenses of the inventions
are known by the United States Approved Names of acofilcon A, alofilcon A,
alphafilcon A, amifilcon A, astifilcon A, atalafilcon A, balafilcon A, bisfilcon A,
bufilcon A, comfilcon, crofilcon A, cyclofiicon A, darfilcon A, deltafilcon A,
deltafilcon B, dimefilcon A, drooxifilcon A, epsifilcon A, esterifilcon A, etafilcon
A, focofilcon A, genfilcon A, govafilcon A, hefilcon A, hefilcon B, hefilcon D,
hilafilcon A, hilafilcon B, hioxifilcon B, hioxifilcon C, hixoifilcon A, hydrofilcon A,
lenefilcon A, licryfilcon A, licryfilcon B, lidofilcon A, lidofilcon B, lotrafilcon A,
lotrafilcon B, mafilcon A, mesifilcon A, methafiicon B, mipafilcon A, nelfilcon A,
netrafilcon A, ocufilcon A, ocufilcon B, ocufilcon C, ocufilcon D, ocufilcon E,
ofilcon A, omafilcon A, oxyfilcon A, pentafilcon A, perfilcon A, pevafilcon A,
phemfilcon A, polymacon, silafilcon A, siloxyfilcon A, tefilcon A, tetrafilcon A,
trifilcon A, and xylofilcon A. More particularly preferred ophthalmic lenses of
the invention are genfilcon A, lenefilcon A, comfilcon, lotrafilcon A, lotraifilcon B,
and balafilcon A. The most preferred lenses include etafilcon A, nelfilcon A,
hilafilcon, and polymacon.
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The term "formulation" refers to the un-po!ymerized mixture of
components used to prepare ophthalmic lenses. These components include
but are not limited to monomers, pre-polymers, diluents, catalysts, initiators
tints, UV blockers, antibacterial agents, polymerization inhibitors, and the like.
These formulations can be polymerized, by thermal, chemical, and light
initiated curing techniques described in the foregoing references as well as
other references in the ophthalmic lens field. As used herein, the terms
"polymerized" or "polymerization" refers to these processes. The preferred
methods of polymerization are the light initiated techniques disclosed in U.S.
Pat. No. 6,822,016 which is hereby incorporated by reference in its entirety.
As used herein the term "treating" refers to physical methods of
contacting the wetting agents and the ophthalmic lens. These methods
exclude placing a drop of a solution containing wetting agent into the eye of an
ophthalmic lens wearer or placing a drop of such a solution onto an ophthalmic
lens prior to insertion of that lens into the eye of a user. Preferably treating
refers to physical methods of contacting the wetting agents with the ophthalmic
lenses prior to selling or otherwise delivering the ophthalmic lenses to a patient.
The ophthalmic lenses may be treated with the wetting agent anytime after they
are polymerized. It is preferred that the polymerized ophthalmic lenses be
treated with wetting agents at temperature of greater than about 50°C. For
example in some processes to manufacture contact lenses, an un-polymerized,
or partially polymerized formulation is placed between two mold halves,
spincasted, or static casted and polymerized. See, U.S. Pat. Nos. 4,495,313;
4,680,336; 4,889,664, 3,408.429; 3,660,545; 4,113,224; and 4,197,266, all of
which are incorporated by reference in their entirety. In the case of hydrogels,
the ophthalmic lens formulation is a hardened disc that is subjected to a
number of different processing steps including treating the polymerized
ophthalmic lens with liquids (such as water, inorganic salts, or organic
solutions) to swell, or otherwise equilibrate this polymerized ophthalmic lens
prior to enclosing the polymerized ophthalmic lens in its final packaging.
Polymerized ophthalmic lenses that have not been swelled or otherwise
equilibrated are known as un-hydrated polymerized ophthalmic lenses. The
addition of the wetting agent to any of the liquids of this "swelling or
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"equilibrating" step at room temperature or below is considered "treating" the
lenses with wetting agents as contemplated by this invention. In addition, the
polymerized un-hydrated ophthalmic lenses may be heated above room
temperature with the wetting agent during swelling or equilibrating steps. The
preferred temperature range is from about 50°C for about 15 minutes to about
sterilization conditions as described below, more preferably from about 50°C to
about 85°C for about 5 minutes.
Yet another method of treating is physically contacting polymerized
ophthalmic lens (either hydrated or un-hydrated) with a wetting agent at
between about room temperature and about 85°C for about 1 minute to about
72 hours, preferably about 24 to about 72 hours, followed by physically
contacting the polymerized ophthalmic lens with a wetting agent at between
about 85°C and 150°C for about 15 minutes to about one hour.
Many ophthalmic lenses are packaged in individual blister packages,
and sealed prior to dispensing the lenses to users. As used herein, these
polymerized lenses are referred to as "hydrated polymerized ophthalmic
lenses". Examples of blister packages and sterilization techniques are
disclosed in the following references which are hereby incorporated by
reference in their entirety, U.S. Pat. Nos. D435.966 S; 4,691,820; 5,467,868;
5,704,468; 5,823,327; 6,050,398, 5,696,686; 6,018,931; 5,577,367; and
5,488,815. This portion of the manufacturing process presents another method
of treating the ophthalmic lenses with wetting agents, namely adding wetting
agents to packaging solution prior to sealing the package, and subsequently
sterilizing the package. This is the preferred method of treating ophthalmic
lenses with wetting agents.
Sterilization can take place at different temperatures and periods of time.
The preferred sterilization conditions range from about 100°C for about 8 hours
to about 150°C for about 0.5 minute. More preferred sterilization conditions
range from about 115°C for about 2.5 hours to about 130°C for about 5.0
minutes. The most preferred sterilization conditions are about 124°C for about
30 minutes.
The "packaging solutions" that are used in methods of this invention may
be water-based solutions. Typical packaging solutions include, without
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WO 2006/088758 PC I7US2006/004877
limitation, saline solutions, other buffered solutions, and deionized water. The
preferred aqueous solution is deioinized water or saline solution containing
salts including, without limitation, sodium chloride, sodium borate, sodium
phosphate, sodium hydrogenphosphate, sodium dihydrogenphosphate, or the
corresponding potassium salts of the same. These ingredients are generally
combined to form buffered solutions that include an acid and its conjugate
base, so that addition of acids and bases cause only a relatively small change
in pH. The buffered solutions may additionally include 2-(N-
morpholino)ethanesulfonic acid (MES), sodium hydroxide, 2,2-
bis(hydroxymethyl)-2,2',2"-nitrilotriethanol, n-tris(hydroxymethyl)methyl-2-
aminoethanesulfonic acid, citric acid, sodium citrate, sodium carbonate, sodium
bicarbonate, acetic acid, sodium acetate, ethylenediamine tetraacetic acid and
the like and combinations thereof. Preferably, the packaging solution is a
borate buffered or phosphate buffered saline solution or deionized water. The
particularly preferred packaging solution contains about 1,850 ppm to about
18,500 ppm sodium borate, most particularly preferred about 3,700 ppm of
sodium borate.
As used here, the term "wetting agent" refers polymers having a number
average molecular weight of about at least 500, that impart a moist feeling
when added to the eyes of contact lens wearers. Examples of preferred
wetting agents include but are not limited to poly(meth)acrylamides [i.e.poly
N,N-dimethylacry!amide), poly (N-methylacrylamide) poly (acrylamide),
poly(N-2-hydroxyethylmethacrylamide), and poly(glucosamineacrylamide)],
poly(itaconic acid), hyaluronic acid, xanthan gum, gum Arabic (acacia), starch,
polymers of hydroxylalkyl(meth)acrylates [i.e. poly( 2-
hydroxyethylmethacrylate), poly(2,3-dihydroxypropylmethacrylate, and poly(2-
hydroxyethylacrylate)], and polyvinylpyrrolidone.
Additional preferred wetting agents include but are not limited to co-
polymers and graft co-polymers of the aforementioned preferred wetting
agents, such co-polymers and graft co-polymers include repeating units of
hydrophilic or hydrophobic monomers, preferably in amounts of about less than
ten percent by weight, more preferably less than about two percent. Such
repeating units of hydrophilic or hydrophobic monomers include but are not
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WO 2006/088758PCT/US2006/004877
limited to alkenes, styrenes, cyclic N-vinyl amides, acrylamides, hydroxyalkyl
(meth) acrylates, alkyl (meth) acrylates, siloxane substituted acrylates, and
siloxane substituted methacrylates. Specific examples of hydrophilic or
hydrophobic monomers which may be used to form the above co-polymers and
graft co-polymers include but are not limited to ethylene, styrene, N-
vinylpyrrolidone, N,N-dimethylacrylamide, 2-hydroxyethylmethyacrylate, methyl
methacrylate and butyl methacrylate, methacryloxypropyl
tristrimethylsiloxysilane and the like. The preferred repeating units of
hydrophilic or hydrophobic monomers are N-vinylpyrrolidone, N,N-
dimethylacrylamide, 2-hydroxyethylmethacrylate, methyl methacrylate, and
mixtures thereof. Further examples of wetting agents include but are not
limited to polymers with carbon backbones and pendant polyethylene glycol
chains [i.e. polymers of polyethylene glycol monoomethacrylate] copolymers of
ethylene glycol [copolymers with 1,2,propyleneglycol, 1,3-propylene glycol,
methyleneglycol, and tetramethylene glycol]. The preferred wetting agents are
polyvinylpyrrolidone, graft co-polymers and co-polymers of polyvinylpyrrolidone,
the particularly preferred wetting agent is polyvinylpyrrolidone.
Polyvinylpyrrolidone ("PVP") is the polymerization product of N-vinyipyrrolidone.
PVP is available in a variety of molecular weights from about 500 to about
6,000,000 Daltons. These molecular weights can be expressed in term of K-
values, based on kinematic viscosity measurements as described in
Encyclopedia of Polymer Science and Engineering, John Wiley & Sons Inc, and
will be expressed in these numbers throughout this application. The use of
PVP having the following K-values from about K-30 to about K-120 is
contemplated by this invention. The more preferred K-values are about K-60 to
about K-100, most preferably about K-80 to about K-100. For the treatment of
etafilcon A lenses, the particularly preferred K-value of PVP is about K-80 to
about K-95, more preferably about K-85 to about K-95, most preferably about
K-90.
The wetting agents can be added to the packaging solution at a variety
of different concentrations such as about 100 ppm to about 150,000 ppm. For
example if the wetting agents are added to packaging solutions containing un-
hydrated polymerized ophthalmic lenses, the wetting agents are preferably
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WO 2006/088758 PCT/US2006/004877
present at a concentration of about 30,000 ppm to about 150,000 ppm. If the
wetting agents are added to packaging solutions containing hydrated
polymerized ophthalmic lenses, the wetting agents are preferably present at a
concentration of about 100 ppm, to about 3000 ppm, more preferably about
200 ppm to about 1000 ppm, most preferably less than about 500 ppm. For
example when etafilcon A lenses are used in this invention and the wetting
agent is K-90 PVP, the preferred packaging solution concentration of PVP K-90
is about 250ppm to about 2,500 ppm, more preferably about 300 to about 500
ppm, most preferably about 350 to about 440 ppm.
When etafilcon A contact lenses are heated with K-90 PVP at a
temperature greater than about 120°C for about 30 minutes at a concentration
of about 400 to about 500 ppm, the treated lenses are more comfortable to
users than untreated lenses. Further, this particular molecular weight and
concentration of PVP does not distort or shift the diameter of the lenses during
the treatment cycle or distort the users vision. While not wishing to be bound
by any particular mechanism of incorporation, it is known that K-90 PVP is
incorporated into the matrix of the lens after it is treated with K-90 PVP. In an
etafilcon A contact lens, the preferred amount of incorporated K-90 PVP is
about 0.01 mg to about 1.0 mg, more preferred about 0.10 mg to about 0.30
mg, most particularly preferred about 0.10 mg to about 0.20 mg. Lenses that
have been treated in this manner are worn by users for up to 12 hours still
maintain the incorporated PVP.
Further the invention includes an ocular device comprising, consisting
essentially of, or consisting of a polymerized ophthalmic lens wherein said
polymerized ophthalmic lens is treated with a wetting agent, provided that the
ophthalmic lens formulation does not comprise said wetting agent prior to its
polymerization. The terms "ophthalmic lens," "wetting agent," "polymerized,"
and "formulation" all have their aforementioned meanings and preferred
ranges. The term "treated" has the equivalent meaning and preferred ranges
as the term treating.
Still further the invention includes an ocular device prepared by treating
a polymerized ophthalmic lens with a wetting agent, provided that the
ophthalmic lens formulation does not comprise said wetting agent prior to its
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WO 2006/088758PCT/US2006/004877
polymerization. The terms "ophthalmic lens," "wetting agent," "polymerized,"
"treated" and "formulation" all have their aforementioned meanings and
preferred ranges.
The application of the invention is described in further detail by use of
the following examples. These examples are not meant to limit the invention,
only to illustrate its use. Other modifications that are considered to be within
the scope of the invention, and will be apparent to those of the appropriate skill
level in view of the foregoing text and following examples.
EXAMPLES
Example 1
Cured etafilcon A contact lenses (sold as 1-Day Acuvue® brand contact
lenses by Johnson & Johnson Vision Care, Inc.) were equilibrated in deionized
water, and packaged in solutions containing PVP in borate buffered saline
solution ((lOOOmL, sodium chloride 3.55g, sodium borate 1.85 g, boric acid
9.26 g, and ethylenediamine tetraacetic acid 0.1 g: 5 rinses over 24 hours,
950 + uL), sealed with a foil lid stock, and sterilized (121°C, 30 minutes).
Before the addition of PVP each solution contained water, l000mL, sodium
chloride 3.55g, sodium borate 1.85 g, boric acid, 9.26 g, and ethylenediamine
tetraacetic acid 0.1g. A variety of different weights and concentrations of PVP
were used as shown in Table 1, below
The amount of PVP that is incorporated into each lens is determined by
removing the lenses from the packaging solution and extracting them with a
mixture 1:1 mixture of N,N-dimethylforamide, (DMF) and deionized water (Dl).
The extracts are evaluated by high performance liquid chromatography
(HPLC). Three lenses were used for each evaluation. The results and their
standard deviation are presented in Table 1.
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WO 2006/088758PCT/US2006/004877
Table 1

Sample # Type of PVP Cone, (ppm) mg of PVPin lens
Control None None none
1 K-12 3000 0.24(0.01)
2 K-12 20,000 1.02(0.01)
3 K-30 1500 1.39(0.05)
4 K-30 2000 1.50(0.01)
5 K-60 1000 0.56(0.00)
6 K-60 1500 0.85(0.02)
7 K-60 2500 1.02(0.03)
8 K-90 250 0.10(0.00)
9 K-90 500 0.14(0.00)
10 K-90 1000 0.2(0.01)
11 K-90 2500 0.25 (0.02)
12 K-120 500 0.07 (0.00)
Example 2
Samples of treated etafilcon A lenses were prepared via the treatment
and sterilization methods of Example 1 from K-12, K-30, K-60, K-90, and K-120
PVP at concentrations of 0.30%, 1.65%, and 3.00%. After sterilization, the
diameter of the lenses was, compared to an untreated lens and evaluated to
determine if the process changed those diameters. The results, Figure 1, plot
the change in diameter vs the type of PVP at a particular concentration. This
data shows that K-12, K-90, and K-120 have a minimal effect on the diameter
of the lenses.
Example 3
Several etafilcon A lenses were treated with K-90 PVP at a
concentration of 500 ppm and sterilized according to the methods of Example
1. The lenses were stored in their packages for approximately 28 days at room
temperature and were then measured for diameter, base curve, sphere power,
and center thickness. Thereafter, lenses were heated at 55°C for one month.
The diameter, base curve, sphere power, and center thickness of the lenses
was measured and the results were evaluated against an untreated lens and
data is presented in Table 2. This data illustrates that the parameters of lenses
treated with K-90 PVP are not significantly affected by time at elevated
temperature.
9

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Table 2

Baseline Change from
Baseline of
Sample after one
month storage at
55 °C
Diameter (mm) 14.37(0.02) 0.02
Base curve (mm) 8.90 (0.03) -0.01
Power (diopter) -0.75 (0.05) 0.00
Center Thickness 0.127(0.005) 0.002
(mm)
Example 4
Etafilcon-A lenses treated with PVP K-90 at a concentration of 440ppm
and sterilized (124°C, approximately 18 minutes) were sampled from
manufacturing lines and measured for diameter, base curve, sphere power,
and center thickness and compared to similar measurements made on
untreated 1-Day Acuvue® brand lenses. The data presented in Table 3
illustrates that K-90 PVP does not significantly affect these parameters.
Table 3

Treated Untreated
Diameter (mm) 14.24 (0.04) 14.18(0.04)
Base curve (mm) 8.94 (0.03) 8.94 (0.04)
Sphere Power Deviation fromTarget (diopter) -0.01 (0.04) -0.02 (0.04)
Center Thickness Deviationfrom Target (mm) 0.000 (0.004) 0.002 (0.005)
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Example 5
Etafilcon A lenses were prepared according to Example 1 at the
concentrations of Table 1. The treated lenses were clinically evaluated in a
double-masked studies of between 9 and 50 patients. The patients wore the
lenses in both eyes for 3-4 days with overnight removal and daily replacement,
and wore untreated 1-Day Acuvue® brand contact lenses for 3-4 days with
overnight removal and daily replacement as a control. Patients were not
allowed to use rewetting drops with either type of lens. Patients were asked to
rate the lens using a questionnaire. All patients were asked a series of
questions relating to overall preference, comfort preference, end of day
preference, and dryness. In their answers they were asked to distinguish if
they preferred the treated lens, the 1-Day control lens, both lenses or neither
lens. The results are shown in Tables 4 and 5. The numbers in the columns
represent the percentage of patients that positively responded to each of the
four options. The "n" number represents the number of patients for a particular
sample type. "DNT" means did not test and n/a means non applicable. The
numbers illustrate that lenses treated with K-90 PVP at a concentration of
about 500 ppm have good clinical comfort on the eye. The sample # refers to
the sample numbers in Table 1.
Table 4

Overall Preference, % Comfort Preference, %
Sample # n PVPtreated 1-Day Both Neither PVPtreated 1-Day Both Neither
1 9 67 22 11 0 67 22 11 0
2 37 27 49 22 3 30 46 19 5

3 41 34 49 15 2 27 56 12 5
4 10 30 20 50 0 30 40 30 0

5 41 27 61 10 2 22 49 29 0
6 42 33 33 33 0 33 29 38 0
7 37 51 27 19 3 49 11 38 3

8 41 27 37 32 5 24 34 37 5
9 48 33 27 40 0 33 23 44 0
10 45 18 27 51 4 16 20 58 7
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WO 2006/088758PCT/US2006/004877
Table 5
Dryness Preference % End of Day Preference %

Sample # n PVPtreated 1-Day Both Neither PVPtreated 1-Day Both Neither
1 9 33 33 11 0 56 22 44 0
2 37 24 43 22 8 27 43 27 5

3 41 32 51 17 2 29 49 17 2
4 10 20 40 30 10 20 10 60 10

5 41 20 46 32 2 20 41 37 2
6 31 42 24 38 0 38 35 16 6
7 42 36 19 38 3 41 24 40 0

8 41 27 22 49 7 22 24 41 7
9 48 38 21 46 0 33 19 44 0
10 45 24 20 58 4 18 20 51 4
Example 6
An etafilcon A contact lens was treated with 500ppm of K-90 PVP using
the methods of Example 1. The treated lenses were briefly rinsed with
phosphate buffered saline solution and rinsed lenses were placed in the well of
a cell culture cluster container (Cellgrow XL) that mimics the dimensions of a
human eye. See, Farris RL, Tear Analysis in Contact Lens Wears, Tr. Am.
Opth. Soc. Vol. LXXXIII, 1985. Four hundred microliters of phosphate buffered
saline solution (KH2PO4 0.20 g/L, KCI- 0.20 g/L, NaCI 8.0 g/L, Na2HPO4
[anhydrous] 1.15 g/L) was added to each container. The wells were covered
and the container was stored in an oven at 35°C.
Three lenses were removed from the oven at various times and
analyzed by HPLC to determine whether PVP was released into the phosphate
buffered saline solution. The average results are presented in Table 6. The
limit of quantification for PVP is 20 ppm. The test did not detect any PVP in the
analyzed samples. This data shows that PVP is not released at levels greater
than 20ppm.
12

WO 2006/088758 PCT/US2006/004877

Tab le 6
Time PVPReleased
30 min. 1 hr. 2hr. 4hr. 8hr. 16 hr. 24 hr 13

WO 2006/088758 PCT/US2006/004877
What is claimed is
1. A method of producing ophthalmic lenses comprising, treating a
polymerized ophthalmic lens with a wetting agent, provided that the ophthalmic
lens formulation does not comprise said wetting agent prior to its
polymerization.
2. The method of claim 1 wherein treating comprises heating the
polymerized ophthalmic lens in a packaging solution.
3. The method of claim 2 wherein the polymerized ophthalmic lens is
heated to a temperature of at least about greater than 50°C to about 150°C.
4. The method of claim 1 wherein the packaging solution comprises
deionized water, or saline solution.
5. The method of claim 1 wherein the packaging solution comprises about
1870 ppm to about 18,700 ppm sodium borate
6. The method of claim 1 wherein the packaging solution comprises about
3700 ppm sodium borate.
7. The method of claim 1 wherein the packaging solution comprises about
2000 ppm to about 5000 ppm sodium borate.
8. The method of claim 1 wherein the wetting agent is selected from the
group consisting of poly(meth)acrylamides, poly(itaconic acid), hyaluronic acid,
xanthan gum, gum Arabic, starch, polymers of hydroxyla!kyl(meth)acrylates,
and polyvinylpyrrolidone.
9. The method of claim 1 wherein the wetting agent is selected from the
group consisting of polyvinylpyrrolidone, graft co-polymers of
polyvinylpyrrolidone, and co-polymers of polyvinylpyrrolidone.
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WO 2006/088758PCT/US2006/004877
10. The method of claim 1 wherein the wetting agent is polyvinylpyrrolidone.
11. The method of claim 10 wherein the K-value of the polyvinylpyrrolidone
is about K-60 to about K-120.
12. The method of claim 10 wherein the K-value of the polyvinylpyrrolidone
is about K-85 to about K-95.
13. The method of claim 10 wherein the K-value of polyvinylpyrrolidone is
about K-90.
14. The method of claim 1 wherein treating comprises heating the
polymerized ophthalmic lens in a packaging solution comprising
polyvinylpyrrolidone having a K-value of about K-85 to about K-95 at a
temperature of greater than about 80°C.
15. The method of claim 1 wherein treating comprises heating the
polymerized ophthalmic lens in a packaging solution comprising
polyvinylpyrrolidone having a K-value of about K-85 to about K-95 at a
temperature of greater than about 120°C.
16. The method of claim 2 wherein the wetting agent is polyvinylpyrrolidone
and the concentration of polyvinylpyrrolidone in the packaging solution is about
250 ppm to about 2500 ppm.
17. The method of claim 2 wherein the concentration of wetting agent in the
packaging solution is about 100 ppm to about 3000 ppm.
18. The method of claim 1 wherein the polymerized ophthalmic lens is
heated at about 124°C for about 18 minutes and with polyvinylpyrrolidone
having a K-value of about K-90 at a concentration of about 400 to about 440
ppm.
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WO 2006/088758PCT/US2006/004877
19. The method of claim 1 wherein the polymerized ophthalmic lens is
heated at about 121 °C for about 30 minutes and with polyvinylpyrrolidone
having a K-value of about K-90 at a concentration of about 300 to about 400
ppm.
20. The method of claim 2 wherein the treating step is conducted in an
individual sealed contact lens package.
21. The method of claim 17 wherein the treating step is conducted in an
individual sealed contact lens package.
22. The method of claim 18 wherein the treating step is conducted in an
individual sealed contact lens package.
23. The method of claim 1 wherein the ophthalmic lens is selected from the
group consisting of acofilcon A, alofilcon A, alphafilcon A, amifilcon A, astifilcon
A, atalafilcon A, balafilcon A, bisfilcon A, bufilcon A, comfilcon, crofilcon A,
cyclofilcon A, darfilcon A, deltafilcon A, deltafilcon B, dimefilcon A, drooxifilcon
A, epsifilcon A, esterifilcon A, etafilcon A, focofilcon A, genfilcon A, govafilcon
A, hefilcon A, hefilcon B, hefilcon D, hilafilcon A, hilafilcon B, hioxifilcon B,
hioxifilcon C, hixoifilcon A, hydrofilcon A, lenefilcon A, licryfilcon A, licryfilcon B,
lidofilcon A, lidofilcon B, lotrafilcon A, lotrafilcon B, mafilcon A, mesifilcon A,
methafilcon B, mipafilcon A, nelfilcon A, netrafilcon A, ocufilcon A, ocufilcon B,
ocufilcon C, ocufilcon D, ocufilcon E, ofilcon A, omafilcon A, oxyfilcon A,
pentafilcon A, perfilcon A, pevafilcon A, phemfilcon A, polymacon, silafilcon A,
siloxyfilcon A, tefilcon A, tetrafilcon A, trifilcon A, and xylofilcon A.
24. The method of claim 2 wherein the ophthalmic lens is selected from the
group consisting of acofilcon A, alofilcon A, alphafilcon A, amifilcon A, astifilcon
A, atalafilcon A, balafilcon A, bisfilcon A, bufilcon A, comfilcon, crofilcon A,
cyclofilcon A, darfilcon A, deltafilcon A, deltafilcon B, dimefilcon A, drooxifilcon
A, epsifilcon A, esterifilcon A, etafilcon A, focofilcon A, genfilcon A, govafilcon
16

WO 2006/088758PCT/US2006/004877
A, hefilcon A, hefilcon B, hefilcon D, hilafilcon A, hilafilcon B, hioxifilcon B,
hioxifilcon C, hixoifilcon A, hydrofilcon A, lenefilcon A, licryfilcon A, licryfilcon B,
lidofilcon A, lidofilcon B, lotrafilcon A, lotrafilcon B, mafilcon A, mesifilcon A,
methafilcon B, mipafilcon A, nelfilcon A, netrafilcon A, ocufilcon A, ocufilcon B,
ocufilcon C, ocufilcon D, ocufilcon E, ofilcon A, omafilcon A, oxyfilcon A,
pentafilcon A, perfilcon A, pevafilcon A, phemfilcon A, polymacon, silafilcon A,
siloxyfilcon A, tefilcon A, tetrafilcon A, trifilcon A, and xylofilcon A.
25. The method of claim 14 wherein the ophthalmic lens is selected from the
group consisting of acofilcon A, alofilcon A, alphafilcon A, amifilcon A, astifilcon
A, atalafilcon A, balafilcon A, bisfilcon A, bufilcon A, comfilcon, crofilcon A,
cyclofilcon A, darfilcon A, deltafilcon A, deltafilcon B, dimefilcon A, drooxifilcon
A, epsifilcon A, esterifilcon A, etafilcon A, focofilcon A, genfilcon A, govafilcon
A, hefilcon A, hefilcon B, hefilcon D, hilafilcon A, hilafilcon B, hioxifilcon B,
hioxifilcon C, hixoifilcon A, hydrofilcon A, lenefilcon A, licryfilcon A, licryfilcon B,
lidofilcon A, lidofilcon B, lotrafilcon A, lotrafilcon B, mafilcon A, mesifilcon A,
methafilcon B, mipafilcon A, nelfilcon A, netrafilcon A, ocufilcon A, ocufilcon B,
ocufilcon C, ocufilcon D, ocufilcon E, ofilcon A, omafilcon A, oxyfilcon A,
pentafilcon A, perfilcon A, pevafilcon A, phemfilcon A, polymacon, silafilcon A,
siloxyfilcon A, tefilcon A, tetrafilcon A, trifilcon A, and xylofilcon A.
26. The method of claim 2 wherein the ophthalmic lens is selected from the
group consisting of genfilcon A, lenefilcon A, lotrafilcon A, lotrafilcon B,
balafilcon A, comfilcon, etafilcon A, nelfilcon A, hilafilcon, and polymacon.
27. The method of claim 14 wherein the ophthalmic lens is selected from the
group consisting of genfilcon A, lenefilcon A, lotrafilcon A, lotrafilcon B,
balafilcon A, comfilcon, etafilcon A, nelfilcon A, hilafilcon, and polymacon.
28. The method of claim 2 wherein the ophthalmic lens is selected from the
group consisting of etafilcon A, nelfilcon A, hilafilcon, and polymacon.
17

WO 2006/088758 PCT/US2006/004877
29. The method of claim 14 wherein the ophthalmic lens is selected from the
group consisting of etafilcon A, nelfilcon A, hilafilcon, and polymacon.
30. The method of claim 2 wherein the ophthalmic lens is selected from the
group consisting of etafilcon A.
31. The method of claim 14 wherein the ophthalmic lens is selected from the
group consisting of etafilcon A.
32. The method of claim 18 wherein the ophthalmic lens is an etafilcon A
contact lens.
33. The method of claim 1 wherein the polymerized ophthalmic lens is an
un-hydrated polymerized ophthalmic lens.
34. The method of claim 33 wherein treating comprises contacting the un-
hydrated polymerized ophthalmic lens with a packaging solution comprises
about 1870 ppm to about 18,700 ppm sodium borate.
35. The method of claim 33 wherein the treating further comprises heating
the un-hydrated polymerized ophthalmic lens and packaging solution to a
temperature of at least about 50°C to about 100°C.
36. The method of claim 33 wherein the treating further comprises
maintaining the un-hydrated polymerized ophthalmic lens and packaging
solution at a temperature of at least about 10°C to about room temperature.
37. The method of claim 34 wherein the packaging solution further
comprises deionized water, or saline solution.
38. The method of claim 33 wherein the wetting agent is selected from the
group consisting of poly(meth)acrylamides, poly(itaconic acid), hyaluronic acid,
18

WO 2006/088758 PCT/US2006/004877
xanthan gum, gum Arabic, starch, polymers of hydroxylalkyl(meth)acrylates,
and polyvinylpyrrolidone.
39. The method of claim 33 wherein the wetting agent is selected from the
group consisting of polyvinylpyrrolidone, graft co-polymers of
polyvinylpyrrolidone, and co-polymers of polyvinylpyrrolidone.
40. The method of claim 33 wherein the wetting agent is
polyvinylpyrrolidone.
41. The method of claim 33 wherein the K-value of the polyvinylpyrrolidone
is about K-60 to about K-120.
42. The method of claim 33 wherein the K-value of the polyvinylpyrrolidone
is about K-60 to about K-90.
43. The method of claim 40 wherein the polyvinylpyrrolidone is present at a
concentration of about 30,000 ppm to about 150,000 ppm.
44. The method of claim 34, further comprising a second step of heating the
un-hydrated polymerized ophthalmic lens of claim 34 with a second portion of
packaging solution comprising a second wetting agent.
45. The method of claim 44 wherein the wetting agent is polyvinylpyrrolidone
having a K-value of about K-60 and the second wetting agent is
polyvinylpyrrolidone having a K-value of about K-90.
46. The method of claim 44 wherein the wetting agent is polyvinylpyrrolidone
having a K-value of about K-90 and the second wetting agent is
polyvinylpyrrolidone having a K-value of about K-90.
19

WO 2006/088758PCT/US2006/004877
47. The method of claim 45 wherein the concentration of K60 is between
about 30,000 ppm and 150,000 about ppm and the concentration of K90 is
between about 100 ppm and about 500 ppm.
48. An ocular device comprising a polymerized ophthalmic lens wherein said
polymerized ophthalmic lens is treated with a wetting agent, provided that the
ophthalmic lens formulation does not comprise said wetting agent prior to its
polymerization.
49. The device of claim 48 wherein the wetting agent is selected from the
group consisting of poly(meth)acry!amides, poly(itaconic acid), hyaluronic acid,
xanthan gum, gum Arabic, starch, polymers of hydroxylalkyl(meth)acrylates,
and polyvinylpyrrolidone.
50. The device of claim 48 wherein the wetting agent is polyvinylpyrrolidone,
graft co-polymers of polyvinylpyrrolidone, and co-polymers of
polyvinylpyrrolidone.
51. The device of claim 48 wherein the wetting agent is polyvinylpyrrolidone.
52. The device of claim 48 comprising about 0.01 mg to about 1.0 mg
polyvinylpyrrolidone.
53. The device of claim 48 comprising about 0.10 mg to about 0.44 mg of
polyvinylpyrrolidone.
54. The device of claim 48 wherein said device does not distort the user's
vision.
55. The device of claim 48 comprising about 0.01 mg to about 1.0 mg of a
wetting agent selected from the group consisting of poly(meth)acrylamides,
poly(itaconic acid), hyaluronic acid, xanthan gum, gum Arabic, starch, polymers
of hydroxylalkyl(meth)acrylates, and polyvinylpyrrolidone.
20

WO 2006/088758PCT/US2006/004877
56. The device of claim 48 comprising about 0.10 mg to about 0.44 mg of
poly(meth)acrylamides, poly(itaconic acid), hyaluronic acid, xanthan gum, gum
Arabic, starch, polymers of hydroxyla!kyl(meth)acrylates, and
polyvinylpyrrolidone.
57. The device of claim 48 wherein said device does not distort the user's
vision.
58. The device of claim 48 wherein said wetting agent remains in the
ophthalmic lens after about 6 hours to about 24 hours of wear by a user.
59. An ocular device prepared by treating a polymerized ophthalmic lens
with a wetting agent, provided that the ophthalmic lens formulation does not
comprise said wetting agent prior to its polymerizaton.
60. The device of claim 59 wherein treating comprises heating the
polymerized ophthalmic lens in a packaging solution to a temperature of about
greater than 50°C to about 150°C.
61. The device of claim 59, wherein the wetting agent is selected from the
group consisting of polyvinylpyrrolidone, graft co-polymers of
polyvinylpyrrolidone, and co-polymers of polyvinylpyrrolidone.
62. The device of claim 59 wherein the wetting agent is polyvinylpyrrolidone
having a K-value of about K-60 to about K-90.
63. The device claim 59 wherein the ophthalmic lens is selected from the
group consisting of acofilcon A, alofilcon A, alphafilcon A, amifilcon A, astifilcon
A, atalafilcon A, balafilcon A, bisfilcon A, bufilcon A, comfilcon, crofilcon A,
cyclofilcon A, darfilcon A, deltafilcon A, deltafilcon B, dimefilcon A, drooxifilcon
A, epsifilcon A, esterifilcon A, etafilcon A, focofilcon A, genfilcon A, govafilcon
A, hefilcon A, hefilcon B, hefilcon D, hilafilcon A, hilafilcon B, hioxifilcon B,
21

WO 2006/088758 PCT/US2006/004877
hioxifilcon C, hixoifilcon A, hydrofilcon A, lenefilcon A, licryfilcon A, licryfilcon B,
lidofilcon A, lidofilcon B, lotrafilcon A, lotrafilcon B, mafilcon A, mesifilcon A,
methafilcon B, mipafilcon A, nelfilcon A, netrafilcon A, ocufilcon A, ocufilcon B,
ocufilcon C, ocufilcon D, ocufilcon E, ofilcon A, omafilcon A, oxyfilcon A,
pentafilcon A, perfilcon A, pevafilcon A, phemfilcon A, polymacon, silafilcon A,
siloxyfilcon A, tefilcon A, tetrafilcon A, trifilcon A, and xylofilcon A.
22
64. The device of claim 59 wherein the ophthalmic lens is selected from the
group consisting of genfilcon A, lenefilcon A, lotrafilcon A, lotrafilcon B,
balifilcon A, comfilcon, etafilcon A, nelfilcon A, hilafilcon, and polymacon.
65. The device of claim 59 wherein the ophthalmic lens is etafilcon A.

This invention relates to comfortable ophthalmic devices and methods of producing.

Documents:

http://ipindiaonline.gov.in/patentsearch/GrantedSearch/viewdoc.aspx?id=8X3efvX/I2phil4VnevfqA==&loc=wDBSZCsAt7zoiVrqcFJsRw==

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Patent Number

268494

Indian Patent Application Number

2592/KOLNP/2007

PG Journal Number

36/2015

Publication Date

04-Sep-2015

Grant Date

31-Aug-2015

Date of Filing

11-Jul-2007

Name of Patentee

JOHNSON & JOHNSON VISION CARE, INC.

Applicant Address

7500 CENTURION PARKWAY, SUITE 100 JACKSONVILLE, FL

Inventors:

#	Inventor's Name	Inventor's Address
1	ROBERT B. STEFFEN	1158 BLUE HERON LANE WEST, JACKSONVILLE BEACH, FL 32250
2	KEVIN P. MCCABE	2843 SHEEPHEAD COURT, SAINT AUGUSTINE, FL 32092
3	HELENE AGUILAR	3217 TRAFALGAR COURT, ST AUGUSTINE, FL 32092
4	SUSAN W. NEADLE	661 BOX BRANCH CIRCLE, JACKSONVILLE, FL 32259
5	ANN-MARIE W. MEYERS (AKA ANN W. MEYERS)	3134 MISTY CREEK LANE, JACKSONVILLE FL 32216
6	DOMINIC GOURD	4428 MILLSTONE COURT, JACKSONVILLE FL 32257
7	KRISTY L. CANAVAN	2326 COMPANION CIRCLE WEST, JACKSONVILLE FL 32224
8	GREGORY A. HILL	1918 HICKORY LANE, ATLANTIC BEACH, FL 32233
9	W. ANTHONY MARTIN	29 JUDSON CIRCLE, ORANGE PARK, FLORIDA 32073
10	DOUGLAS G. VANDERLAAN (AKA DOUG G. VANDERLAAN)	1453 N. MARKET STREET, JACKSONVILLE FL 32206

PCT International Classification Number

A61L 12/14

PCT International Application Number

PCT/US2006/004877

PCT International Filing date

2006-02-10

PCT Conventions:

#	PCT Application Number	Date of Convention	Priority Country
1	60/652,809	2005-02-14	U.S.A.
2	60/695,783	2005-06-30	U.S.A.